The Hypericum genus contains over 450 species; the minority that have been chemically analyzed to date are rich in secondary metabolites such as flavonoids, xanthones, anthrones, dianthrones, and various benzophenone derivatives. Several of these species, most commonly Hypericum perforatum, are used as herbal treatments for anti-inflammatory, antibacterial, antiviral, and anti-depressive applications (Mennini, T. and M. Gobbi (2004), “The antidepressant mechanism of Hypericum perforatum” Life Sciences 75(9):1021; and Rocha, L., A. Marston, et al. (1995), “Antibacterial phloroglucinols and flavonoids from Hypericum brasiliense” Phytochemistry 40(5):1447). The chemical diversity within this single species may explain these multiple medicinal uses. Phloroglucinols are of particular interest since they have multiple bioactivities themselves, including anti-bacterial activity (Rocha, L., et al. (1995)) and anti-depressive properties in humans (Laakmann, G.; Schuele, C.; Baghai, T.; Kieser, M. (1998), “St. John's wort in mild to moderate depression: the relevance of hyperforin for the clinical efficacy,” Pharmacopsychiatry 31 (Suppl. 1), 54-59). A few known phloroglucinols found in Hypericum species include hyperforin, uliginosin A and B; and hyperbrasilol A, B, and C (Rocha, L., et al. (1995)).
Anti-inflammatory activity in mammals has been reported for more than one species from the Hypericum genus (Rabanal, R. M., C. X. Bonkanka, et al. (2005), “Analgesic and topical anti-inflammatory activity of Hypericum canariense L. and Hypericum glandulosum Ait,” Journal of Ethnopharmacology 96(3):591; and Sanchez-Mateo, C. C., C. X. Bonkanka, et al. (2006), “Evaluation of the analgesic and topical anti-inflammatory effects of Hypericum reflexum L. fil,” Journal of Ethnopharmacology 107(1):1); however, it is not known whether this is caused by the same compound(s) in these different species. This anti-inflammatory activity has been confirmed by both in vivo and in vitro studies in Hypericum and related genuses (Rabanal, R. M., C. X. Bonkanka, et al. (2005); and Yamakuni, T., K. Aoki, et al. (2006), “Garcinone B reduces prostaglandin E2 release and NF-[kappa]B-mediated transcription in C6 rat glioma cells,” Neuroscience Letters 394(3):206). Extracts or compounds from Hypericum species H. perforatum, H. laricifolium, and H. patulum (El-Seedi, Hesham R., Ringbom, T., Torssell, K. and Lars Bohlin. (2003), “Constituents of Hypericum laricifolium and Their Cyclooxygenase (COX) Enzyme Activities,” Chem. Pharm. Bull. 51:1439-1440), reduce cyclooxygenase activity and inducible nitrous oxide synthase activity in vitro (Raso, G. M., M. Pacilio, et al. (2002), “In-vivo and in-vitro anti-inflammatory effect of Echinacea purpurea and Hypericum perforatum,” Journal of Pharmacy and Pharmacology 54:1379), indicating their direct effect on reducing inflammation.
A few North American species of Hypericum have been used historically for their medical properties; one such species is H. gentianoides (Hamel, Paul B., Chiltoskey, Mary U. 1975 Cherokee Plants and Their Uses—A 400 Year History, Sylva, N.C. Herald Publishing Co. 53 p). H. gentianoides (orangegrass) is a small perennial that is native to much of the eastern United States. The Cherokee Native Americans used this plant for the treatment of fever, gastrointestinal disorders, nosebleeds, sores, and venereal disease (Hamel, Paul B., et al. 1975). Despite its use by Native Americans, there has been very little biochemical research on this species.